Ethanol → HCID 178469421, compound

HRID 1838950Notes

Reaction equation

HRID 1838950 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:15](O)[CH3:16]>>[OH:1][C:2]1[N:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:15][CH3:16])=[O:5]

Participants

3

Reactant 2

HCID 702EthanolHCID 178524662HCID 178524662, compound

Product 1

HCID 178469421HCID 178469421, compoundYield 74%

Conditions

Temperature
80 °C

Procedure

2-Hydroxy-5-sulfonicotinic acid (500 g, 2.28 mol) was dissolved in ethanol (2.5 L) with stirring and heated to 80° C. After 30mins 0.5 L of solvent was distilled off, then replaced with fresh ethanol (0.5 L) and taken back to 80° C. After a further 60 mins 1.0 L of solvent was distilled off, then replaced with fresh ethanol (1.0 L) and taken back to 80° C. After a further 60 mins 1.0 L of solvent was distilled off, the reaction cooled to 22° C. and stirred for 16 hr. The precipitated product was filtered, washed with ethanol (0.5 L) and dried at 50° C. under vacuum to afford the title compound (416 g, 74%) as a white solid. Decomposition pt 237° C. δ (DMSOd 6): 1.25 (3H, t), 4.19 (2H, q), 7.66 (1H, d), 8.13 (1H, d). m/z (Found:248 [M+H]+, 100%. C8H10NO6S requires 248.22).

Workup

  1. distillationAfter 30mins 0.5 L of solvent was distilled off
  2. customtaken back to 80° C
  3. distillationAfter a further 60 mins 1.0 L of solvent was distilled off
  4. customtaken back to 80° C
  5. distillationAfter a further 60 mins 1.0 L of solvent was distilled off
  6. temperaturethe reaction cooled to 22° C.
  7. stirringstirred for 16 hr
  8. filtrationThe precipitated product was filtered
  9. washwashed with ethanol (0.5 L)
  10. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-e25a4a40d5e74dd7b483623f7df5120b
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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